Isolation and identification of chlorinated genistein from Actinoplanes sp. HBDN08 with antioxidant and antitumor activities.
Isolation and identification of chlorinated genistein from Actinoplanes sp. HBDN08 with antioxidant and antitumor activities.
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DOI：
10.1021/jf9035194
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发表时间：
2010-02
影响因子：
6.1
通讯作者：
W. Xiang;Ji Zhang;Jidong Wang;Ling Jiang;B. Jiang;Z. Xiang;Xiangjing Wang
中科院分区：
文献类型：
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作者：
W. Xiang;Ji Zhang;Jidong Wang;Ling Jiang;B. Jiang;Z. Xiang;Xiangjing Wang
Actinoplanes sp. 菌株。使用来自卤化酶基因保守区域的引物通过PCR引导的方法筛选HBDN08。从 Actinoplanes sp. 的发酵液中分离出一种新的氯化异黄酮，3',8-二氯金雀异黄酮 (1) 和 8-氯金雀异黄酮 (2)。 HBDN08。它们的结构在广泛的 1D 和 2D NMR 以及 HRESI-MS、ESI-MS、UV 和 IR 光谱分析的基础上得到了阐明。还通过高效液相色谱（HPLC）分析研究了这两种化合物的来源。结果表明，它们不是生物合成的，而是来自游动动线菌对金雀异黄酮的生物转化。 HBDN08。通过脂质过氧化测定评估分离的化合物1和2的抗氧化活性。根据对人乳腺癌细胞系MDA-MB-231的细胞增殖抑制率计算其抗肿瘤活性。结果表明，化合物1 (IC(50) = 5.2 microM)和2 (IC(50) = 7.5 microM)比金雀异黄素(IC(50) = 13.6 microM)表现出更强的抗氧化活性。与染料木黄酮的抗肿瘤活性相比，化合物1和2的抗肿瘤活性分别增加了7.7倍和2.6倍。这些结果表明，PCR 引导的筛选策略是获得产生卤代代谢物的菌株的快速方法。此外，这些结果表明氯化对金雀异黄酮的生物活性有显着影响。这可能是研究金雀异黄酮结构-活性关系的重要信息。
A strain Actinoplanes sp. HBDN08 was screened by PCR-guided method using primers derived from conserved regions of halogenase genes. A new chlorinated isoflavone, 3',8-dichlorogenistein (1), along with 8-chlorogenistein (2) were isolated from the fermentation broth of Actinoplanes sp. HBDN08. Their structures were elucidated on the basis of extensive 1D and 2D NMR as well as HRESI-MS, ESI-MS, UV, and IR spectroscopic analyses. The origin of the two compounds was also investigated by high-performance liquid chromatography (HPLC) analysis. The results demonstrated that they were not biosynthesized but derived from the biotransformation of genistein by Actinoplanes sp. HBDN08. The antioxidant activities of the isolated compounds 1 and 2 were evaluated by using the lipid peroxidation assay. Their antitumor activities were calculated according to the inhibitory rate of cell proliferation against the human breast cancer cell line MDA-MB-231. The results indicated that compounds 1 (IC(50) = 5.2 microM) and 2 (IC(50) = 7.5 microM) showed stronger antioxidant activities than genistein (IC(50) = 13.6 microM). In comparison with the antitumor activities of genistein, those of compounds 1 and 2 increased 7.7- and 2.6-fold, respectively. These results suggest that the PCR-guided screening strategy is a rapid method for obtaining halometabolite-producing strains. Moreover, these results reveal that chlorination has significant effects on the bioactivities of genistein. This could be important information for studying the structure-activity relationships of genistein.